organic compounds - (IUCr) Crystallography Journals Onlinejournals.iucr.org/e/issues/2008/02/00/ng2418/ng2418.pdf4-(9-Anthryl)-2-methylbutyn-2-ol Irena Bylin´ska, Artur Sikorski*

4-(9-Anthryl)-2-methylbutyn-2-ol

Irena Bylinska, Artur Sikorski* and Wiesław Wiczk

Faculty of Chemistry, University of Gdansk, J. Sobieskiego 18, 80-952 Gdansk,

Poland

Correspondence e-mail: [email protected]

Received 10 January 2008; accepted 15 January 2008

Key indicators: single-crystal X-ray study; T = 298 K; mean �(C–C) = 0.005 A;

R factor = 0.052; wR factor = 0.170; data-to-parameter ratio = 13.7.

There are two molecules in the asymmetric unit of the title

compound, C19H16O. Neighbouring molecules are linked

through O—H� � �O hydrogen bonds into an R44(8) ring motif.

There are also C—H� � �� hydrogen and �–� interactions. The

molecules are either parallel to each other or are inclined at an

angle of 12.5 (1)�.

Related literature

For applications of this class of compounds, see: Bunz (2000);

De Silva et al. (1999), Krasovitski & Bolotin (1988); O’Regan

& Gratzel (1991); Schumm et al. (1994). For the use of

ethynylanthracene derivatives in organic synthesis, see Wen et

al. (2004); Xiao et al. (2007). For comparison bond dimensions

of the anthracene skeleton, see: Cuffet et al. (2005); Elangovan

et al. (2005). For the structure of 9,10-bis(3-hydroxy-3-methyl-

1-butyne)anthracene, see: Dang et al. (2002).

Experimental

Crystal data

C19H16OMr = 260.32Triclinic, P1a = 9.995 (2) Ab = 12.738 (3) A

c = 12.905 (3) A� = 75.70 (3)�

� = 72.18 (3)�

� = 68.84 (3)�

V = 1441.4 (7) A3

Z = 4Mo K� radiation� = 0.07 mm�1

T = 298 (2) K0.60 � 0.20 � 0.10 mm

Data collection

Kuma KM-4 diffractometerAbsorption correction: none5258 measured reflections5011 independent reflections2370 reflections with I > 2�(I)

Rint = 0.0193 standard reflections

every 200 reflectionsintensity decay: 1.1%

Refinement

R[F 2 > 2�(F 2)] = 0.051wR(F 2) = 0.170S = 0.985011 reflections

366 parametersH-atom parameters constrained��max = 0.25 e A�3

��min = �0.34 e A�3

Table 1Hydrogen-bond geometry (A, �).

D—H� � �A D—H H� � �A D� � �A D—H� � �A

O18—H18� � �O38i 0.82 2.01 2.726 (3) 145O38—H38� � �O18ii 0.82 2.06 2.766 (3) 145

Symmetry codes: (i) �xþ 1;�yþ 1;�zþ 1; (ii) xþ 1; y� 1; z.

Table 2C—H� � �� interactions (A,�).

Cg1 is the centroid of the C5/C10–C14 ring and Cg2 is the centroid of the C1–C4/C12/C11 ring.

X H J H� � �J X� � �J X—I� � �J

C19 H19C Cg1iii 2.87 3.810 (4) 167C20 H20B Cg2iii 2.76 3.703 (4) 168C24 H24 Cg2iv 2.64 3.472 (3) 149C25 H25 Cg1iv 2.92 3.794 (3) 157

Symmetry codes: (iii) 1� y, �y, 1� z; (iv) 1� x, 1� y, �z.

Table 3�–� interactions (A,�).

Cg3 is the centroid of the C25/30–C34 ring and Cg4 is the centroid of the C26-C29/C33/C34 ring. The dihedral angle is that between the planes of the ringsCgI and CgJ. The interplanar distance is the perpendicular distance of CgIfrom ring J. The offset is the perpendicular distance of ring I from ring J.

CgI CgJ Cg� � �Cg Dihedral angle Interplanar distance Offset

3 4v 3.794 (2) 1.2 3.370 (2) 1.336 (2)4 3v 3.794 (2) 1.2 3.404 (2) 1.464 (2)

Symmetry code: (v) 1� x, �y, �z.

Data collection: KM-4 Software (Oxford Diffraction, 1995-2003);

cell refinement: KM-4 Software; data reduction: KM-4 Software;

program(s) used to solve structure: SHELXS97 (Sheldrick, 2008);

program(s) used to refine structure: SHELXL97 (Sheldrick, 2008);

molecular graphics: ORTEPII (Johnson, 1976); software used to

prepare material for publication: SHELXL97 and PLATON (Spek,

2003).

This work was financially supported by the Ministry of

Science and Higher Education (Poland) under grant BW 8000-

5-0408-7.

organic compounds

o484 Bylinska et al. doi:10.1107/S1600536808001542 Acta Cryst. (2008). E64, o484–o485

Acta Crystallographica Section E

Structure ReportsOnline

ISSN 1600-5368

http://crossmark.crossref.org/dialog/?doi=10.1107/S1600536808001542&domain=pdf&date_stamp=2008-01-23

Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: NG2418).

References

Bunz, U. H. F. (2000). Chem. Rev. 100, 1605–1644.Cuffet, L., Hudson, R. D. A., Gallagher, J. F., Jennings, S., McAdam, C. J.,

Connelly, R. B. T., Manning, A. R., Robinson, B. H. & Simpson, J. (2005).Organometallics, 24, 2051–2060.

Dang, H., Levitus, M. & Garcia-Garibay, M. A. (2002). J. Am. Chem. Soc. 124,136–143.

De Silva, A. P., Dixon, I. M., Gunaratne, H. Q. N., Gunnlaugsson, T., Maxwell,P. R. S. M. & Rice, T. E. (1999). J. Am. Chem. Soc. 121, 1393–1394.

Elangovan, A., Kao, K.-M., Yang, S.-W., Chen, Y.-L., Ho, T.-I. & Su, Y. O.(2005). J. Org. Chem. 35, 4460–4469.

Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge NationalLaboratory, Tennessee, USA.

Krasovitski, B. M. & Bolotin, B. M. (1988). Organic Luminescent Materials.Weinheim: VCH.

O’Regan, B. & Gratzel, M. (1991). Nature (London), 353, 737–738.Oxford Diffraction (1995–2003). KM4 Software. Version 1.171. Oxford

Diffraction Poland, Wrocław, Poland.Schumm, J. S., Pearson, D. L. & Tour, J. M. (1994). Angew. Chem. Int. Ed. Engl.

33, 1360–1363.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.Wen, J. Y., Chang, H. K., Mi-Yun, J., Seung, K. L., Ming, J. P., Seung, J. J. &

Bong, R. C. (2004). Chem. Mater. 16, 2783–2789.Xiao, Q., Ranasinghe, R. T., Tang, A. M. P. & Brown, T. (2007). Tetrahedron,

63, 3483–3490.

organic compounds

Acta Cryst. (2008). E64, o484–o485 Bylinska et al. � C19H16O o485

supporting information

sup-1Acta Cryst. (2008). E64, o484–o485


Acta Cryst. (2008). E64, o484–o485 [doi:10.1107/S1600536808001542]


Irena Bylińska, Artur Sikorski and Wiesław Wiczk

S1. Comment

Recently there is a need for molecules containing triple bond because of their electroconductive, magnetic and nonlinear

optical properties. This class of the compounds are used as molecular wires (Bunz, 2000), molecular scale logic gates (De

Silva et al., 1999), optical and microelectronic devices (Schumm et al., 1994), sensors (Krasovitski & Bolotin, 1988) and

molecular photovoltaic cells (O′Regan & Grätzel, 1991)). Ethynylanthracene derivatives are substrates in many synthesis

(Wen et al., 2004; Xiao et al., 2007). 2-Methyl-3-butyn-2-ol is an alternative protecting group for (trimethylsilyl)acetyl-

ene, more useful in reaction carried at higher temperature (because of its higher boiling point) as well as giving acetylene

derivatives containing various substituents in homo- and heterocoupling. Because of that we use this protecting group to

synthesize acetylene derivatives to study influence of the aromatic subtituent size on the photophysical properties of the

compounds in search for organic material with extended π system, characterized by high fluorescence quantum yield. As

an intermediate in the synthesis of anthracene derivative, 9-(3-hydroxy-3-methyl-1-butyne)anthracene was isolated and

its crystal structure was determined.

Parameters characterizing the geometry of the anthracene skeleton are typical of anthracene-based derivatives (Cuffet et

al., 2005; Elangovan et al., 2005).

In the crystal, the asymmetric unit consists of two molecules of the title compound (Fig. 1) which crystallizing in the

triclinic crystal system, in P -1 space group, as well as 9,10-bis(3-hydroxy-3-methyl-1-butyne)anthracene (Dang et al.,

2002).

In the crystal structure, neighbouring molecules are linked through O—H···O hydrogen bond forming R44(8) ring motif

(Table 1 and Fig. 2). Molecules which forming this motif are linked by C—H···π hydrogen bonds (Table 2 and Fig. 2) or

π-π interactions (Table 3 and Fig. 2). In the packing, the anthracene moieties are either parallel or inclined at an angle of

12.5 (1)°.

S2. Experimental

9-(3-hydroxy-3-methyl-1-butyne)anthracene has been synthesized by Sonogashira-Hagihara coupling from 9-bromo-

anthracene (10 mmol) and 2-methyl-3-butyn-2-ol (20 mmol) in DMF in the presence of Pd(PPh3)4 (0.0162 mmol) and

Cu2I2 (0.13 mmol) as catalysts, triphenylphosphine (0.16 mmol), triethylamine (12 ml). The mixture was stirred at 333 K

under argon atmosphere for 24 h. The reaction was monitored by TLC (petroleum ether-ethyl/acetate 10:1 v/v, Rf=0.64;

Merck Silica-gel plates (Kieselgel 60 F254)). When the reaction was completed the catalysts were filtered off, filtrate was

poured into water and extracted with ethyl acetate. The brownish-red organic layer was dried over anhydrous MgSO4.

The solvent was removed in vacuo giving a brownish-red oil. The crude was isolated by column chromatography on

silica gel (Merck, Silica gel 60, 0.040–0.063 mm) using petroleum ether-ethyl/acetate (10:1 v/v) as an eluent and then

crystallized from ethyl acetate to give yellow crystals (79% yield) [m.p. = 400–402 K].



S3. Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H distances of 0.93 Å and with

Uiso(H) = 1.2Ueq(C) (C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for the methyl group) and O—H distances of 0.82 Å and

with Uiso(H) = 1.5Ueq(C).

Figure 1

The molecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at

the 25% probability level and H atoms are shown as small spheres of arbitrary radii. Cg1, Cg2, Cg3 and Cg4 denote the

ring centroids.



Figure 2

The arrangement of the ions in the unit cell, viewed along the c axis, showing R44(8) ring motifs. The O—H···O

interactions are represented by dashed lines, and C—H···π and π-π interactions by dotted lines. H atoms not involved in

interactions have been ommited. [Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1 + x, -1 + y, z; (iii) 1 - x, -y, 1 - z; (iv) 1 - x, -

y, -z; (v) 1 - x, -y, -z.]


Crystal data

C19H16OMr = 260.32Triclinic, P1Hall symbol: -P 1a = 9.995 (2) Åb = 12.738 (3) Åc = 12.905 (3) Åα = 75.70 (3)°β = 72.18 (3)°γ = 68.84 (3)°V = 1441.4 (7) Å3

Z = 4F(000) = 552Dx = 1.200 Mg m−3

Mo Kα radiation, λ = 0.71073 ÅCell parameters from 50 reflectionsθ = 2.2–25.0°µ = 0.07 mm−1

T = 298 KBlock, white0.60 × 0.20 × 0.10 mm

Data collection

Kuma KM4 diffractometer

Radiation source: fine-focus sealed tubeGraphite monochromatorθ/2θ scans5258 measured reflections

5011 independent reflections2370 reflections with I > 2σ(I)Rint = 0.019θmax = 25.0°, θmin = 2.2°h = −11→11k = −14→14



l = 0→153 standard reflections every 200 reflections

intensity decay: 1.1%

Refinement

Refinement on F2

Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.051wR(F2) = 0.170S = 0.985011 reflections366 parameters0 restraintsPrimary atom site location: structure-invariant

direct methodsSecondary atom site location: difference Fourier

map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrainedw = 1/[σ2(Fo

2) + (0.0961P)2 + 0.1391P] where P = (Fo

2 + 2Fc2)/3

(Δ/σ)max < 0.001Δρmax = 0.25 e Å−3

Δρmin = −0.34 e Å−3

Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4

Extinction coefficient: 0.036 (4)

Special details

Experimental. noGeometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq

C1 0.6439 (3) 0.6352 (3) 0.2744 (3) 0.0703 (8)H1 0.6036 0.6730 0.3353 0.084*C2 0.7751 (4) 0.6414 (3) 0.2076 (3) 0.0873 (10)H2 0.8236 0.6839 0.2227 0.105*C3 0.8389 (4) 0.5848 (3) 0.1160 (3) 0.0878 (11)H3 0.9293 0.5897 0.0705 0.105*C4 0.7694 (3) 0.5232 (3) 0.0939 (3) 0.0767 (9)H4 0.8133 0.4850 0.0333 0.092*C5 0.5568 (3) 0.4561 (2) 0.1365 (2) 0.0635 (8)H5 0.6000 0.4182 0.0757 0.076*C6 0.3395 (4) 0.3939 (3) 0.1734 (3) 0.0737 (9)H6 0.3822 0.3552 0.1130 0.088*C7 0.2042 (4) 0.3938 (3) 0.2325 (3) 0.0816 (10)H7 0.1533 0.3565 0.2125 0.098*C8 0.1392 (4) 0.4496 (3) 0.3240 (3) 0.0763 (9)H8 0.0442 0.4507 0.3643 0.092*C9 0.2129 (3) 0.5021 (2) 0.3547 (2) 0.0626 (8)H9 0.1693 0.5364 0.4178 0.075*C10 0.4290 (3) 0.5670 (2) 0.3197 (2) 0.0519 (7)C11 0.5670 (3) 0.5725 (2) 0.2536 (2) 0.0549 (7)C12 0.6313 (3) 0.5154 (2) 0.1606 (2) 0.0571 (7)C13 0.3538 (3) 0.5062 (2) 0.2937 (2) 0.0497 (6)C14 0.4198 (3) 0.4511 (2) 0.1999 (2) 0.0565 (7)



C15 0.3608 (3) 0.6290 (2) 0.4102 (2) 0.0528 (7)C16 0.3033 (3) 0.6851 (2) 0.4820 (2) 0.0508 (7)C17 0.2380 (3) 0.7569 (2) 0.5676 (2) 0.0473 (6)O18 0.1648 (2) 0.86882 (14) 0.52019 (15) 0.0609 (5)H18 0.1476 0.9139 0.5618 0.091*C19 0.1281 (3) 0.7122 (3) 0.6591 (2) 0.0733 (9)H19A 0.0470 0.7163 0.6316 0.110*H19B 0.0921 0.7572 0.7173 0.110*H19C 0.1748 0.6344 0.6869 0.110*C20 0.3575 (3) 0.7670 (3) 0.6081 (3) 0.0732 (9)H20A 0.4249 0.7962 0.5474 0.110*H20B 0.4098 0.6932 0.6413 0.110*H20C 0.3145 0.8178 0.6618 0.110*C21 0.8461 (3) 0.1228 (3) 0.0840 (3) 0.0745 (9)H21 0.8929 0.0796 0.1399 0.089*C22 0.9110 (4) 0.1911 (3) 0.0040 (3) 0.0928 (11)H22 1.0007 0.1960 0.0063 0.111*C23 0.8464 (4) 0.2547 (3) −0.0822 (3) 0.0838 (10)H23 0.8933 0.3008 −0.1378 0.101*C24 0.7175 (4) 0.2495 (2) −0.0849 (2) 0.0675 (8)H24 0.6750 0.2926 −0.1429 0.081*C25 0.5086 (3) 0.1752 (2) −0.0037 (2) 0.0576 (7)H25 0.4649 0.2187 −0.0610 0.069*C26 0.2985 (3) 0.1032 (3) 0.0763 (3) 0.0709 (9)H26 0.2533 0.1480 0.0201 0.085*C27 0.2306 (4) 0.0359 (3) 0.1544 (3) 0.0865 (10)H27 0.1392 0.0347 0.1520 0.104*C28 0.2958 (4) −0.0326 (3) 0.2399 (3) 0.0811 (10)H28 0.2477 −0.0790 0.2940 0.097*C29 0.4271 (3) −0.0314 (3) 0.2436 (2) 0.0646 (8)H29 0.4701 −0.0785 0.3000 0.078*C30 0.6386 (3) 0.0447 (2) 0.1664 (2) 0.0496 (6)C31 0.7097 (3) 0.1152 (2) 0.0851 (2) 0.0527 (7)C32 0.6432 (3) 0.1807 (2) −0.0028 (2) 0.0533 (7)C33 0.5030 (3) 0.0397 (2) 0.1639 (2) 0.0509 (7)C34 0.4362 (3) 0.1077 (2) 0.0770 (2) 0.0547 (7)C35 0.7051 (3) −0.0211 (2) 0.2548 (2) 0.0573 (7)C36 0.7636 (3) −0.0706 (2) 0.3274 (2) 0.0573 (7)C37 0.8328 (3) −0.1305 (2) 0.4196 (2) 0.0559 (7)O38 0.9388 (2) −0.07847 (15) 0.41664 (16) 0.0645 (6)H38 0.9901 −0.1179 0.4596 0.097*C39 0.9208 (4) −0.2512 (2) 0.4034 (3) 0.0831 (11)H39A 0.9937 −0.2516 0.3347 0.125*H39B 0.8560 −0.2911 0.4026 0.125*H39C 0.9690 −0.2881 0.4626 0.125*C40 0.7207 (4) −0.1233 (3) 0.5257 (3) 0.0870 (11)H40A 0.6651 −0.0449 0.5313 0.130*H40B 0.7689 −0.1558 0.5853 0.130*



H40C 0.6552 −0.1644 0.5293 0.130*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

C1 0.059 (2) 0.082 (2) 0.072 (2) −0.0160 (16) −0.0187 (16) −0.0192 (17)C2 0.063 (2) 0.114 (3) 0.092 (3) −0.034 (2) −0.019 (2) −0.021 (2)C3 0.052 (2) 0.127 (3) 0.080 (2) −0.026 (2) −0.0044 (18) −0.023 (2)C4 0.0560 (19) 0.102 (3) 0.0614 (19) −0.0108 (17) −0.0111 (15) −0.0175 (17)C5 0.066 (2) 0.0655 (18) 0.0487 (16) −0.0035 (15) −0.0127 (14) −0.0175 (14)C6 0.091 (3) 0.069 (2) 0.0673 (19) −0.0273 (18) −0.0207 (19) −0.0149 (16)C7 0.098 (3) 0.081 (2) 0.082 (2) −0.050 (2) −0.015 (2) −0.0135 (19)C8 0.082 (2) 0.074 (2) 0.075 (2) −0.0402 (18) −0.0072 (18) −0.0058 (18)C9 0.070 (2) 0.0516 (17) 0.0559 (17) −0.0165 (14) −0.0066 (15) −0.0040 (13)C10 0.0499 (16) 0.0473 (14) 0.0472 (15) −0.0010 (12) −0.0148 (12) −0.0046 (12)C11 0.0484 (17) 0.0554 (16) 0.0547 (16) −0.0031 (13) −0.0208 (13) −0.0065 (13)C12 0.0517 (17) 0.0650 (17) 0.0479 (15) −0.0064 (13) −0.0155 (13) −0.0103 (13)C13 0.0552 (16) 0.0411 (13) 0.0448 (14) −0.0081 (12) −0.0141 (12) 0.0000 (12)C14 0.0618 (18) 0.0518 (16) 0.0489 (16) −0.0089 (14) −0.0169 (14) −0.0038 (13)C15 0.0551 (16) 0.0451 (15) 0.0520 (16) −0.0062 (12) −0.0163 (13) −0.0066 (14)C16 0.0510 (16) 0.0478 (15) 0.0505 (15) −0.0094 (12) −0.0146 (13) −0.0081 (14)C17 0.0502 (15) 0.0398 (14) 0.0510 (15) −0.0076 (11) −0.0191 (12) −0.0064 (12)O18 0.0694 (13) 0.0396 (10) 0.0797 (13) −0.0064 (8) −0.0369 (10) −0.0116 (9)C19 0.078 (2) 0.079 (2) 0.0551 (17) −0.0200 (17) −0.0087 (16) −0.0109 (16)C20 0.071 (2) 0.0691 (19) 0.091 (2) −0.0075 (15) −0.0479 (18) −0.0183 (17)C21 0.065 (2) 0.085 (2) 0.077 (2) −0.0254 (17) −0.0344 (17) 0.0080 (18)C22 0.071 (2) 0.111 (3) 0.101 (3) −0.044 (2) −0.033 (2) 0.015 (2)C23 0.080 (2) 0.090 (2) 0.078 (2) −0.038 (2) −0.0195 (19) 0.0091 (19)C24 0.076 (2) 0.0655 (19) 0.0596 (18) −0.0212 (16) −0.0258 (16) 0.0034 (15)C25 0.0621 (19) 0.0519 (16) 0.0553 (16) −0.0027 (14) −0.0327 (14) −0.0013 (13)C26 0.0574 (19) 0.076 (2) 0.084 (2) −0.0115 (16) −0.0340 (17) −0.0128 (17)C27 0.0499 (19) 0.112 (3) 0.100 (3) −0.0241 (19) −0.0234 (18) −0.015 (2)C28 0.066 (2) 0.105 (3) 0.077 (2) −0.041 (2) −0.0083 (18) −0.0102 (19)C29 0.070 (2) 0.0683 (19) 0.0545 (17) −0.0186 (15) −0.0169 (15) −0.0090 (14)C30 0.0517 (16) 0.0496 (15) 0.0488 (15) −0.0073 (12) −0.0228 (12) −0.0087 (12)C31 0.0480 (16) 0.0565 (16) 0.0526 (15) −0.0089 (13) −0.0198 (13) −0.0078 (13)C32 0.0556 (17) 0.0497 (15) 0.0510 (15) −0.0077 (13) −0.0223 (13) −0.0028 (13)C33 0.0509 (16) 0.0525 (15) 0.0464 (15) −0.0076 (12) −0.0162 (13) −0.0096 (12)C34 0.0497 (16) 0.0564 (16) 0.0592 (16) −0.0061 (13) −0.0226 (13) −0.0148 (14)C35 0.0625 (18) 0.0565 (16) 0.0545 (16) −0.0120 (13) −0.0278 (14) −0.0033 (13)C36 0.0665 (18) 0.0537 (16) 0.0572 (16) −0.0168 (13) −0.0281 (14) −0.0043 (13)C37 0.0611 (18) 0.0561 (17) 0.0563 (16) −0.0114 (13) −0.0347 (14) −0.0032 (13)O38 0.0616 (12) 0.0555 (11) 0.0874 (14) −0.0091 (9) −0.0470 (11) −0.0072 (10)C39 0.121 (3) 0.0475 (17) 0.088 (2) −0.0088 (17) −0.059 (2) −0.0052 (16)C40 0.089 (2) 0.103 (3) 0.061 (2) −0.026 (2) −0.0264 (18) 0.0053 (18)



Geometric parameters (Å, º)

C1—C2 1.348 (4) C21—C22 1.341 (4)C1—C11 1.407 (4) C21—C31 1.397 (4)C1—H1 0.9300 C21—H21 0.9300C2—C3 1.397 (5) C22—C23 1.388 (4)C2—H2 0.9300 C22—H22 0.9300C3—C4 1.343 (5) C23—C24 1.325 (4)C3—H3 0.9300 C23—H23 0.9300C4—C12 1.409 (4) C24—C32 1.404 (4)C4—H4 0.9300 C24—H24 0.9300C5—C12 1.373 (4) C25—C32 1.375 (4)C5—C14 1.378 (4) C25—C34 1.375 (4)C5—H5 0.9300 C25—H25 0.9300C6—C7 1.334 (5) C26—C27 1.336 (5)C6—C14 1.417 (4) C26—C34 1.401 (4)C6—H6 0.9300 C26—H26 0.9300C7—C8 1.391 (5) C27—C28 1.399 (5)C7—H7 0.9300 C27—H27 0.9300C8—C9 1.346 (4) C28—C29 1.333 (4)C8—H8 0.9300 C28—H28 0.9300C9—C13 1.400 (4) C29—C33 1.419 (4)C9—H9 0.9300 C29—H29 0.9300C10—C11 1.398 (4) C30—C33 1.390 (4)C10—C13 1.407 (4) C30—C31 1.397 (4)C10—C15 1.426 (4) C30—C35 1.427 (3)C11—C12 1.416 (4) C31—C32 1.421 (3)C13—C14 1.411 (4) C33—C34 1.420 (3)C15—C16 1.185 (4) C35—C36 1.180 (3)C16—C17 1.453 (4) C36—C37 1.466 (3)C17—O18 1.425 (3) C37—O38 1.426 (3)C17—C20 1.498 (4) C37—C40 1.479 (4)C17—C19 1.500 (4) C37—C39 1.500 (4)O18—H18 0.8200 O38—H38 0.8200C19—H19A 0.9600 C39—H39A 0.9600C19—H19B 0.9600 C39—H39B 0.9600C19—H19C 0.9600 C39—H39C 0.9600C20—H20A 0.9600 C40—H40A 0.9600C20—H20B 0.9600 C40—H40B 0.9600C20—H20C 0.9600 C40—H40C 0.9600

C2—C1—C11 121.2 (3) C22—C21—C31 121.3 (3)C2—C1—H1 119.4 C22—C21—H21 119.4C11—C1—H1 119.4 C31—C21—H21 119.4C1—C2—C3 120.7 (3) C21—C22—C23 121.0 (3)C1—C2—H2 119.7 C21—C22—H22 119.5C3—C2—H2 119.7 C23—C22—H22 119.5C4—C3—C2 119.9 (3) C24—C23—C22 119.7 (3)



C4—C3—H3 120.0 C24—C23—H23 120.1C2—C3—H3 120.0 C22—C23—H23 120.1C3—C4—C12 121.4 (3) C23—C24—C32 122.0 (3)C3—C4—H4 119.3 C23—C24—H24 119.0C12—C4—H4 119.3 C32—C24—H24 119.0C12—C5—C14 121.9 (3) C32—C25—C34 122.5 (2)C12—C5—H5 119.1 C32—C25—H25 118.8C14—C5—H5 119.1 C34—C25—H25 118.8C7—C6—C14 121.9 (3) C27—C26—C34 121.5 (3)C7—C6—H6 119.1 C27—C26—H26 119.2C14—C6—H6 119.1 C34—C26—H26 119.2C6—C7—C8 119.9 (3) C26—C27—C28 120.6 (3)C6—C7—H7 120.0 C26—C27—H27 119.7C8—C7—H7 120.0 C28—C27—H27 119.7C9—C8—C7 120.5 (3) C29—C28—C27 119.9 (3)C9—C8—H8 119.7 C29—C28—H28 120.0C7—C8—H8 119.7 C27—C28—H28 120.0C8—C9—C13 121.4 (3) C28—C29—C33 121.9 (3)C8—C9—H9 119.3 C28—C29—H29 119.1C13—C9—H9 119.3 C33—C29—H29 119.1C11—C10—C13 120.4 (2) C33—C30—C31 121.1 (2)C11—C10—C15 119.5 (3) C33—C30—C35 119.7 (3)C13—C10—C15 120.0 (2) C31—C30—C35 119.2 (2)C10—C11—C1 122.4 (3) C30—C31—C21 123.2 (2)C10—C11—C12 119.4 (3) C30—C31—C32 119.1 (2)C1—C11—C12 118.2 (3) C21—C31—C32 117.7 (3)C5—C12—C4 121.9 (3) C25—C32—C24 122.7 (2)C5—C12—C11 119.5 (3) C25—C32—C31 119.0 (3)C4—C12—C11 118.7 (3) C24—C32—C31 118.3 (3)C9—C13—C10 122.5 (3) C30—C33—C29 123.4 (2)C9—C13—C14 118.4 (3) C30—C33—C34 119.1 (2)C10—C13—C14 119.0 (3) C29—C33—C34 117.5 (3)C5—C14—C13 119.8 (3) C25—C34—C26 122.3 (3)C5—C14—C6 122.4 (3) C25—C34—C33 119.2 (2)C13—C14—C6 117.8 (3) C26—C34—C33 118.6 (3)C16—C15—C10 176.9 (3) C36—C35—C30 176.2 (3)C15—C16—C17 177.3 (3) C35—C36—C37 178.5 (3)O18—C17—C16 108.37 (19) O38—C37—C36 107.7 (2)O18—C17—C20 106.5 (2) O38—C37—C40 110.3 (2)C16—C17—C20 109.6 (2) C36—C37—C40 110.7 (2)O18—C17—C19 109.2 (2) O38—C37—C39 105.0 (2)C16—C17—C19 110.9 (2) C36—C37—C39 110.5 (2)C20—C17—C19 112.1 (2) C40—C37—C39 112.4 (3)C17—O18—H18 109.5 C37—O38—H38 109.5C17—C19—H19A 109.5 C37—C39—H39A 109.5C17—C19—H19B 109.5 C37—C39—H39B 109.5H19A—C19—H19B 109.5 H39A—C39—H39B 109.5C17—C19—H19C 109.5 C37—C39—H39C 109.5



H19A—C19—H19C 109.5 H39A—C39—H39C 109.5H19B—C19—H19C 109.5 H39B—C39—H39C 109.5C17—C20—H20A 109.5 C37—C40—H40A 109.5C17—C20—H20B 109.5 C37—C40—H40B 109.5H20A—C20—H20B 109.5 H40A—C40—H40B 109.5C17—C20—H20C 109.5 C37—C40—H40C 109.5H20A—C20—H20C 109.5 H40A—C40—H40C 109.5H20B—C20—H20C 109.5 H40B—C40—H40C 109.5

C11—C1—C2—C3 −0.5 (5) C31—C21—C22—C23 −1.6 (6)C1—C2—C3—C4 0.0 (6) C21—C22—C23—C24 1.1 (6)C2—C3—C4—C12 0.8 (5) C22—C23—C24—C32 −0.2 (5)C14—C6—C7—C8 −1.0 (5) C34—C26—C27—C28 −0.1 (5)C6—C7—C8—C9 −1.2 (5) C26—C27—C28—C29 −0.2 (6)C7—C8—C9—C13 2.5 (5) C27—C28—C29—C33 1.2 (5)C13—C10—C11—C1 177.9 (2) C33—C30—C31—C21 −179.8 (3)C15—C10—C11—C1 1.6 (4) C35—C30—C31—C21 1.7 (4)C13—C10—C11—C12 −0.6 (4) C33—C30—C31—C32 −1.5 (4)C15—C10—C11—C12 −176.9 (2) C35—C30—C31—C32 −179.9 (2)C2—C1—C11—C10 −178.2 (3) C22—C21—C31—C30 179.6 (3)C2—C1—C11—C12 0.3 (4) C22—C21—C31—C32 1.3 (5)C14—C5—C12—C4 −178.1 (3) C34—C25—C32—C24 −179.9 (3)C14—C5—C12—C11 0.6 (4) C34—C25—C32—C31 −0.6 (4)C3—C4—C12—C5 177.6 (3) C23—C24—C32—C25 179.3 (3)C3—C4—C12—C11 −1.0 (4) C23—C24—C32—C31 −0.1 (5)C10—C11—C12—C5 0.3 (4) C30—C31—C32—C25 1.8 (4)C1—C11—C12—C5 −178.2 (3) C21—C31—C32—C25 −179.8 (3)C10—C11—C12—C4 179.0 (2) C30—C31—C32—C24 −178.9 (2)C1—C11—C12—C4 0.5 (4) C21—C31—C32—C24 −0.4 (4)C8—C9—C13—C10 175.6 (3) C31—C30—C33—C29 179.2 (3)C8—C9—C13—C14 −1.7 (4) C35—C30—C33—C29 −2.4 (4)C11—C10—C13—C9 −177.3 (2) C31—C30—C33—C34 0.0 (4)C15—C10—C13—C9 −1.0 (4) C35—C30—C33—C34 178.4 (2)C11—C10—C13—C14 0.0 (3) C28—C29—C33—C30 178.8 (3)C15—C10—C13—C14 176.3 (2) C28—C29—C33—C34 −2.0 (4)C12—C5—C14—C13 −1.2 (4) C32—C25—C34—C26 179.4 (3)C12—C5—C14—C6 177.5 (3) C32—C25—C34—C33 −0.9 (4)C9—C13—C14—C5 178.3 (2) C27—C26—C34—C25 179.0 (3)C10—C13—C14—C5 0.9 (3) C27—C26—C34—C33 −0.7 (4)C9—C13—C14—C6 −0.4 (3) C30—C33—C34—C25 1.2 (4)C10—C13—C14—C6 −177.8 (2) C29—C33—C34—C25 −178.0 (3)C7—C6—C14—C5 −177.0 (3) C30—C33—C34—C26 −179.1 (3)C7—C6—C14—C13 1.7 (4) C29—C33—C34—C26 1.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

O18—H18···O38i 0.82 2.01 2.726 (3) 145



O38—H38···O18ii 0.82 2.06 2.766 (3) 145

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y−1, z.

Documents

organic compounds - (IUCr) Crystallography Journals Onlinejournals.iucr.org/e/issues/2008/02/00/ng2418/ng2418.pdf4-(9-Anthryl)-2-methylbutyn-2-ol Irena Bylin´ska, Artur Sikorski*